US4822508A - Shear stable multirange oils having an improved viscosity index - Google Patents

Shear stable multirange oils having an improved viscosity index Download PDF

Info

Publication number
US4822508A
US4822508A US07/248,233 US24823388A US4822508A US 4822508 A US4822508 A US 4822508A US 24823388 A US24823388 A US 24823388A US 4822508 A US4822508 A US 4822508A
Authority
US
United States
Prior art keywords
methacrylic acid
carbon atoms
esters
alcohols
percent
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US07/248,233
Other languages
English (en)
Inventor
Horst Pennewiss
Heinz Jost
Helmut Knoell
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Roehm GmbH Darmstadt
Original Assignee
Roehm GmbH Darmstadt
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Roehm GmbH Darmstadt filed Critical Roehm GmbH Darmstadt
Assigned to ROHM GMBH, 6100 DARMSTADT, FED. REP. OF GERMANY reassignment ROHM GMBH, 6100 DARMSTADT, FED. REP. OF GERMANY ASSIGNMENT OF ASSIGNORS INTEREST. Assignors: JOST, HEINZ, KNOELL, HELMUT, PENNEWISS, HORST
Application granted granted Critical
Publication of US4822508A publication Critical patent/US4822508A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M145/00—Lubricating compositions characterised by the additive being a macromolecular compound containing oxygen
    • C10M145/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M145/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate
    • C10M145/12—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate monocarboxylic
    • C10M145/14—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/10—Esters
    • C08F220/12—Esters of monohydric alcohols or phenols
    • C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
    • C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
    • C08F220/1804—C4-(meth)acrylate, e.g. butyl (meth)acrylate, isobutyl (meth)acrylate or tert-butyl (meth)acrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/04—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
    • C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M149/10—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
    • C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
    • C10M2209/084—Acrylate; Methacrylate
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/022—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group
    • C10M2217/023—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amino group the amino group containing an ester bond
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/024—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/02—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds
    • C10M2217/028—Macromolecular compounds obtained from nitrogen containing monomers by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a nitrogen-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2217/00—Organic macromolecular compounds containing nitrogen as ingredients in lubricant compositions
    • C10M2217/06—Macromolecular compounds obtained by functionalisation op polymers with a nitrogen containing compound

Definitions

  • the present invention relates to multirange lubricating oils having high shear stability, and in particular gear oils, comprising paraffinic oils as their base, which lubricating oils contain from 3 to 60 percent by weight of an additive improving their viscosity index, said additive comprising esters of acrylic acid or of methacrylic acid.
  • esters of acrylic acid and methacrylic acid with linear alcohols having from 6 to 15 carbon atoms (a) esters of acrylic acid and methacrylic acid with linear alcohols having from 6 to 15 carbon atoms,
  • esters of acrylic acid and methacrylic acid with linear C 16 -C 30 alcohols (b) esters of acrylic acid and methacrylic acid with linear C 16 -C 30 alcohols
  • esters of acrylic acid and methacrylic acid with branched C 8 -C 40 alcohols (c) esters of acrylic acid and methacrylic acid with branched C 8 -C 40 alcohols
  • esters of acrylic acid and methacrylic acid with C 1 -C 5 alcohols (d) esters of acrylic acid and methacrylic acid with C 1 -C 5 alcohols
  • component (b) representing not more than 5 mole percent of said polymer
  • component (b') representing from 10 to 70 mole percent of said polymers.
  • Polymers P 1 and P 2 are dissolved in a solvent.
  • the additives of this European patent act not only as pour point improvers, but also influence the viscosity characteristics of the oils as a function of temperature, at both high and low temperatures. They were developed for the purpose of providing additives which bring the performance properties of the so called “critical base oils” (that is, lower quality base oils, dewaxed to a lesser degree), which have lately been appearing on the market, into line with practical requirements.
  • critical base oils that is, lower quality base oils, dewaxed to a lesser degree
  • a special group of lubricating oils are the multirange lubricating oils having high shear resistance (high stability to shear), and particularly those used as gear oils. (Cf. Ullmanns Encyklopaedie der ischen Chemie, loc. cit., pp. 591-606.)
  • multirange lubricating oils having high shear stability will satisfy the practical requirements for gear oils particularly well if they contain as additives a mixture of from 10 to 20 percent, and preferably from 12 to 18 percent, by weight of the multirange oils, of at least two different polymer species, P, each of these polymers species being composed of monomers selected from the group consisting of
  • esters of methacrylic acid and acrylic acid with linear alcohols having 6 to 15 carbon atoms (a) esters of methacrylic acid and acrylic acid with linear alcohols having 6 to 15 carbon atoms,
  • esters of methacrylic acid and acrylic acid with linear alcohols having from 16 to 30 carbon atoms (b) esters of methacrylic acid and acrylic acid with linear alcohols having from 16 to 30 carbon atoms,
  • esters of methacrylic acid and acrylic acid with branched alcohols having from 6 to 40 carbon atoms (c) esters of methacrylic acid and acrylic acid with branched alcohols having from 6 to 40 carbon atoms,
  • esters of methacrylic acid and acrylic acid with alcohols having from 1 to 5 carbon atoms (d) esters of methacrylic acid and acrylic acid with alcohols having from 1 to 5 carbon atoms, and
  • Monomer or monomers (a) are from 0 to 100 mole percent of said polymers; monomer(s) (b) are from 0 to 10 mole percent, monomers (c), (d) and (e) combined are from 0 to 100 mole percent, and monomers (a) to (e) combined are 100 mole percent of each species, with the condition that the individual polymer species P 1 , P 2 , and possible further species, P n , differ from one another by at least 10 mole percent with respect to their content of component (a).
  • the effect of the mixtures of the polymer species P 1 , P 2 , and so forth according to the invention is superior to the effect of each of the components used by itself.
  • monomer component (a) represents from 10 to 100 mole percent; component (b) from 0 to 5 mole percent, and more particularly from 2 to 4 mole percent; component (c) from 0 to 90 mole percent, and more particularly from 20 to 60 mole percent; component (d) from 0 to 50 mole percent, and more particularly from 5 to 30 mole percent; and component (e) from 0 to 20 mole percent, and more particularly from 0 to 10 mole percent, of the individual polymer species P 1 , P 2 and optional further species P 3 , P 4 , P 5 , P n .
  • esters of acrylic acid or methacrylic acid with linear C 10 -C 14 alcohols produced for example by the Ziegler process through hydrolysis of aluminum alkoxides, are preferred.
  • esters of acrylic acid or methacrylic acid with linear C 10 -C 14 alcohols produced for example by the Ziegler process through hydrolysis of aluminum alkoxides.
  • These include, for example, certain of the alcohol products commercially available in various grades under the trademarks "Lorole” (Henkel AG, Duesseldorf) and "Alfole” (Condea, Hamburg).
  • the components (b) are preferably acrylate or methacrylate esters of linear C 16 -C 24 alcohols, and more particularly C 16 -C 20 alcohols. Examples are tallow fatty alcohols and alcohol grades sold under the "Alfole" mark.
  • the components (c) are preferably esters of acrylic acid or of methacrylic acid with branched C 8 -C 20 alcohols of the isoalkanol type, and particularly with isodecyl, isotridecyl, and isooctadecyl alcohols.
  • the ester of acrylic acid or of methacrylic acid with "Dobanol 25L” (a product of Shell-Chemie), for example, should be used proportionately as both component (a) and component (c).
  • Components (a), (b), (c), (d) and (e), in turn, may be grafted onto polyolefins or onto olefin copolymers (OCP).
  • the multirange lubricating oils of the invention having high shear stability may further contain from 0.05 to 1.0 percent, by weight of the multirange oils, of additives improving their pour point (see below).
  • the average molecular weights of the polymers P generally range from 20,000 to 100,000, as determined by gel permeation chromatography.
  • the polymers P 1 , P 2 , etc. can be produced by polymerization of monomers (a) to (e) by the usual free radical initiated polymerization processes according to the desired composition.
  • Component (e) of the polymers P should be understood to mean, by definition, monomers susceptible of free radical polymerization and containing functional groups in the molecule, and more particularly those monomers which are known to have a positive dispersant and detergent action in oil additives. Nitrogen-containing monomers of this kind are particularly taught in U.S. Pat. No. 3,067,163 which is incorporated herein by reference. Illustrative of these are, for example, compounds of the formula ##STR1## wherein R 1 is hydrogen or methyl and Bs is an inert heterocyclic five- or six-membered ring or ##STR2## wherein Z is oxygen or a --NR 4 group.
  • Q is a linear or branched aliphatic hydrocarbon bridge having from 2 to 10 carbon atoms
  • R 2 and R 3 taken alone are each alkyl having from 1 to 6 carbon atoms or, taken together with the nitrogen atom and inclusive of other possible hetero atoms, form a heterocyclic five- or six-membered ring
  • R 4 is hydrogen or alkyl having from 1 to 6 carbon atoms.
  • Examples of such monomers are C-vinyl- and N-vinyl-pyridine, C- and N-vinylpyrrolidone, C- and N-vinylcarbazole and C- and N-vinylimidazole, as well as their alkyl derivatives, particularly the N-vinyl compounds, and moreover, the dialkylaminoalkyl esters of acrylic acid and of methacrylic acid, particularly dimethylaminoethyl acrylate and methacrylate and dimethylaminopropyl acrylate and methacrylate, as well as the corresponding amides (dialkylaminoalkyl acrylamides and methacrylamides), for example dimethylaminopropyl acrylamide and methacrylamide.
  • the multirange lubricating oils having high shear resistance having high shear resistance
  • multirange lubricating oils having high shear resistance within the meaning of the present invention are multigrade gear oils, and in particular those of SAE classification 75 W-90. (Compare SAE J 306 C.) Further details on SAE classification will be found in DIN 51 511 and 51 512, for example.
  • Suitable paraffinic base oils are those having a viscosity from 3 to 8 mm 2 /sec at 100° C., and particularly mixtures of the fractions NS 100/NS 150.
  • Such paraffinic base oils are known in the art and are discussed in Ullmanns Encyklopaedie der ischen Chemie, 4th ed., Vol. 20, pp. 487-503, or in Alphonse Schilling, "Motor Oils and Engine Lubrication", 2nd ed., 1968, pp. 2.2 to 2.21, for example.
  • Additives improving the pour point which may be added to the multirange lubricating oils of the invention having high shear stability are, in particular, polyalkyl acrylates and methacrylates having C 12 -C 18 alkyl groups, for example those marketed by Rohm GmbH under the marks "Viscoplex" 1-31, 1-33, and 1-35.
  • the polymers can be produced by prior art polymerization processes. (See Houben-Weyl, 4th ed., Vol. XIV.)
  • a mixture of mineral oil and of a monomer mixture composed as desired of (a), (b), (c), (d), and (e) is charged into a reaction vessel appropriately equipped with stirrer, thermometer, reflux condenser, and metering line.
  • the charge is heated to about 90° C. to 100° C. under a carbon dioxide atmosphere and with stirring.
  • an initiator preferably a peroxy compound such as a perester or peroxide, or an azo compound
  • a chain transfer agent e.g. a mercapto compound such as dodecyl mercaptan (Cf. Brandrup-Immergut, Polymer Handbook, 2nd ed., J.
  • a mixture of the monomers (a), (b), (c), (d) and (e) and more initiator and optional chain transfer agent is metered in. About 2 hours after completion of this addition, still more initiator and optional chain transfer agent are fed in.
  • the total amount of initiator usually is from 0.5 to 3 percent, and the amount of chain transfer agent from 0.1 to 2.0 percent, both by weight of the total amount of monomers.
  • the total polymerization time generally is between 8 and 9 hours.
  • a viscous solution with a polymer content that usually ranges from 40 to 70 percent by weight is obtained.
  • One of the components is charged into a suitable container and heated to about 80° C. to 120° C. with stirring.
  • the components to be admixed are likewise heated to about 80° C. to 120° C. and are added to the initially charged component as rapidly as possible with stirring.
  • the additives improving the viscosity index is dissolved in the base oil together with any further additives, such as a detergent-inhibitor package, at 50° C. to 60° C. with stirring.
  • Such detergent-inhibitor packages ordinarily contain corrosion inhibitors, dispersants and/or detergents comprising (a) hydrophilic polar groups such as sulfonate, hydroxy, mercapto, carboxyl, or carbonamide groups, (2) hydrophobic (oleophilic) aliphatic, cycloaliphatic, or alkylaromatic hydrocarbon residues which impart oil solubility, and (3) one or more metal ions or amino groups.
  • hydrophilic polar groups such as sulfonate, hydroxy, mercapto, carboxyl, or carbonamide groups
  • hydrophobic (oleophilic) aliphatic, cycloaliphatic, or alkylaromatic hydrocarbon residues which impart oil solubility
  • metal ions or amino groups one or more metal ions or amino groups.
  • Exemplary dispersants/detergents include metal naphthenates and metal stearates and salts of alkylaryl sulfonic acids, phenoxides and phenoxide-sulfides, phosphates, thiophosphates, phosphonates, thiophosphonates, carbamates, thiocarbamates, compounds of polyisobutene and succinic acid, fumarates, etc.
  • the packages may also contain anti-wear agents or friction modifiers such as fatty acids or their esters, particularly with C 12 -C 18 alcohols; fatty alcohols; N-acylated sarcosine; and sulfated natural fats; used alone or in combination with phosphonic acids.
  • anti-wear agents or friction modifiers such as fatty acids or their esters, particularly with C 12 -C 18 alcohols; fatty alcohols; N-acylated sarcosine; and sulfated natural fats; used alone or in combination with phosphonic acids.
  • the packages may also contain oxidation inhibitors such as sterically hindered phenols.
  • the multirange lubricating oils of the invention are used particularly as gear oils.
  • Viscosity (100° C., 72.5 wt. %): 800 mm 2 /sec
  • Polymer content 71.0 wt. %
  • Viscosity (100° C., 71.0 wt. % ): 460 mm 2 /sec
  • Viscosity (100° C., 72.5 wt. %): 800 mm 2 /sec

Landscapes

  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Lubricants (AREA)
US07/248,233 1985-12-13 1988-09-19 Shear stable multirange oils having an improved viscosity index Expired - Lifetime US4822508A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3544061 1985-12-13
DE19853544061 DE3544061A1 (de) 1985-12-13 1985-12-13 Hochscherstabile mehrbereichsschmieroele mit verbessertem viskositaetsindex

Related Parent Applications (1)

Application Number Title Priority Date Filing Date
US06937199 Continuation 1986-12-02

Publications (1)

Publication Number Publication Date
US4822508A true US4822508A (en) 1989-04-18

Family

ID=6288340

Family Applications (1)

Application Number Title Priority Date Filing Date
US07/248,233 Expired - Lifetime US4822508A (en) 1985-12-13 1988-09-19 Shear stable multirange oils having an improved viscosity index

Country Status (5)

Country Link
US (1) US4822508A (ja)
EP (1) EP0225598B1 (ja)
JP (1) JP2509199B2 (ja)
CA (1) CA1288411C (ja)
DE (2) DE3544061A1 (ja)

Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4921625A (en) * 1988-06-27 1990-05-01 Shell Oil Company Method for preparing functionalized block copolymers
US4968444A (en) * 1983-10-28 1990-11-06 Rohm Gmbh Lubricating oil additives
EP0436872A2 (de) * 1990-01-12 1991-07-17 Röhm GmbH Kraftübertragungsflüssigkeit auf Basis Mineralöl
US5035822A (en) * 1986-06-13 1991-07-30 Institut Francais Du Petrol Copolymer compositions particularly useful as additives for hydrocarbon oils
US5043087A (en) * 1986-04-25 1991-08-27 Rohn Gmbh Addives for paraffinic lubricants
US5073600A (en) * 1989-10-12 1991-12-17 Shell Oil Company Dispersant viscosity index improvers
US5188770A (en) * 1989-09-09 1993-02-23 Rphm GmbH Viscosity index improver having detergent properties
US5349019A (en) * 1988-12-24 1994-09-20 Hoechst New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils
US5368761A (en) * 1993-04-30 1994-11-29 Rohm And Haas Company Copolymer useful as a pour point depressant for a lubricating oil
US5416162A (en) * 1993-09-20 1995-05-16 Rohm And Haas Company Compatibilizer for a viscosity index improving polymer blend
US5520832A (en) * 1994-10-28 1996-05-28 Exxon Research And Engineering Company Tractor hydraulic fluid with wide temperature range (Law180)
US5534175A (en) * 1992-12-28 1996-07-09 The Lubrizol Corporation Copolymers of unsaturated fatty esters, their use as viscosity improver and lubricating oil containing said copolymers
AU674927B2 (en) * 1992-12-28 1997-01-16 Lubrizol Corporation, The Copolymers of unsaturated fatty esters, their use as viscosity improver and lubricating oil containing said copolymers
US5622924A (en) * 1994-03-08 1997-04-22 Sanyo Chemical Industries, Ltd. Viscosity index improver and lubricating oil
US5665685A (en) * 1994-06-02 1997-09-09 Sanyo Chemical Industries, Ltd. Gear and transmission lubricant compositions of improved sludge-dispersibility, fluids comprising the same
US5696066A (en) * 1994-10-12 1997-12-09 Rohm And Haas Company Additive for lubricating oil
RU2102402C1 (ru) * 1990-12-14 1998-01-20 Министеро делл Юниверсита е делла Ричерка Шентифика е Текнологика Полимерная присадка, улучшающая индекс вязкости, способ ее получения, мономер, обладающий диспергирующим действием, концентрат и смазочное масло
US5807815A (en) * 1997-07-03 1998-09-15 Exxon Research And Engineering Company Automatic transmission fluid having low Brookfield viscosity and high shear stability
US5821313A (en) * 1995-06-19 1998-10-13 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
EP0937769A1 (en) * 1998-02-18 1999-08-25 The Lubrizol Corporation Viscosity improvers for lubricating oil compositions
US5969068A (en) * 1995-06-19 1999-10-19 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US6124249A (en) * 1998-12-22 2000-09-26 The Lubrizol Corporation Viscosity improvers for lubricating oil compositions
KR100405388B1 (ko) * 1994-10-19 2004-02-11 아깊페트롤리쏘시에떼퍼아 찌오니 불소탄성중합체와 상용성인 윤활유용 다기능성 첨가제
US20040254080A1 (en) * 2003-06-10 2004-12-16 The Lubrizol Corporation, A Corporation Of The State Of Ohio Functionalized polymer composition for grease
EP1619235A1 (en) * 2004-07-21 2006-01-25 Afton Chemical Limited Polyalkylmethacrylate polymer as filtration improver
US20100120641A1 (en) * 2007-06-08 2010-05-13 Toho Chemical Industry Co., Ltd. Pour point depressant for lubricant
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
CN102858928A (zh) * 2010-04-26 2013-01-02 赢创罗曼克斯添加剂有限公司 传动系统用润滑剂
WO2013062924A2 (en) 2011-10-27 2013-05-02 The Lubrizol Corporation Lubricating composition containing an esterified polymer
US20150075061A1 (en) * 2013-09-17 2015-03-19 Vanderbilt Chemicals, Llc Method of reducing aqueous separation in an emulsion composition suitable for engine fueled by e85 fuel
US9051529B2 (en) 2009-06-04 2015-06-09 The Lubrizol Corporation Lubricating composition containing friction modifier and viscosity modifier
US9481849B2 (en) 2010-04-26 2016-11-01 Evonik Oil Additives Gmbh Polymer useful as viscosity index improver
US20220372388A1 (en) * 2019-12-12 2022-11-24 Evonik Operations Gmbh High viscosity polyacrylate base fluids

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3607444A1 (de) * 1986-03-07 1987-09-10 Roehm Gmbh Additive fuer mineraloele mit stockpunktverbessernder wirkung
DE3889533T2 (de) * 1987-08-19 1994-12-01 Pennzoil Prod Co Giesspunkterniedrigende methacrylatadditive und -zusammensetzungen.
FR2660661B1 (fr) * 1990-04-09 1994-04-15 Norsolor Nouveaux polymeres acryliques et leur application a la formulation de peintures et d'adhesifs en solvant.
FR2701036B1 (fr) * 1993-02-04 1995-04-21 Great Lakes Chemical France Additif de viscosité stable au cisaillement pour huiles lubrifiantes.
US20040077509A1 (en) * 2002-08-02 2004-04-22 Tsuyoshi Yuki Viscosity index improver and lube oil containing the same
CN101932226B (zh) 2008-03-05 2013-10-30 星天具工业株式会社 割草机用旋转切割器
WO2009125075A1 (fr) * 2008-04-11 2009-10-15 Total Raffinage Marketing Fluide lubrifiant multifonctionnel
CA2809816C (en) * 2010-08-31 2019-06-04 The Lubrizol Corporation Star polymer and lubricating composition thereof
WO2012076285A1 (en) * 2010-12-10 2012-06-14 Evonik Rohmax Additives Gmbh A lubricant composition
US10149597B2 (en) * 2013-06-26 2018-12-11 Electrolux Appliances Aktiebolag Cutlery basket for a dishwasher
US20180066200A1 (en) 2015-03-03 2018-03-08 Basf Se Pib as high viscosity lubricant base stock
JP2017186539A (ja) * 2016-03-30 2017-10-12 三洋化成工業株式会社 潤滑油組成物
CN116710541A (zh) 2020-11-25 2023-09-05 雪佛龙日本有限公司 润滑油组合物
WO2023084360A1 (en) 2021-11-09 2023-05-19 Chevron Japan Ltd. High efficiency engine oil compositions

Citations (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2091627A (en) * 1934-06-08 1937-08-31 Rohm & Haas Composition of matter and process
US2100993A (en) * 1934-12-14 1937-11-30 Rohm & Haas Process for preparing esters and products
US2114233A (en) * 1933-05-22 1938-04-12 Rohm & Haas Polymeric materials
US2655479A (en) * 1949-01-03 1953-10-13 Standard Oil Dev Co Polyester pour depressants
US3067163A (en) * 1958-05-22 1962-12-04 Rohm & Haas Preparation of detergent oil-additive graft copolymers by delayed addition of nitrogen-containing comonomer to a partially polymerized long chain alkyl or vinyl ester and product obtained thereby
US3226326A (en) * 1962-07-30 1965-12-28 Shell Oil Co Lubricating composition
US3598736A (en) * 1967-08-30 1971-08-10 Shell Oil Co Polyalkylmethacrylates as pour point depressants for lubricating oils
US3607749A (en) * 1967-12-05 1971-09-21 British Petroleum Co Viscosity index improvers
DE2258966A1 (de) * 1971-12-03 1973-06-07 Shell Int Research Schmieroelgemische
US3788990A (en) * 1971-12-22 1974-01-29 J Elliott Lubricating compositions
US3817866A (en) * 1972-11-24 1974-06-18 Texaco Inc Alkylacrylate alkanediol methacrylate interpolymers and pour depressed compositions thereof
US3833501A (en) * 1971-12-22 1974-09-03 Burmah Oil Trading Ltd Lubricating compositions
US3869396A (en) * 1971-05-05 1975-03-04 Shell Oil Co Lubricating oil compositions
US3951929A (en) * 1972-05-08 1976-04-20 Texaco Inc. Polyacrylates and waxy residual fuel compositions thereof
US4073738A (en) * 1976-01-28 1978-02-14 Basf Aktiengesellschaft Lubricating oil compositions containing alkyl acrylate or methacrylate polymers and copolymers of styrene and conjugated diene
US4149984A (en) * 1977-09-08 1979-04-17 Rohm Gmbh Lubricating oil additives
GB1559952A (en) * 1977-10-26 1980-01-30 Shell Int Research Lubricating oil compositions
US4282132A (en) * 1978-08-11 1981-08-04 Rohm Gmbh Lubricating oil additives
US4290925A (en) * 1979-02-16 1981-09-22 Rohm Gmbh Lubricating oil additives
US4332689A (en) * 1979-09-28 1982-06-01 Nippon Oil And Fats Co., Ltd. Water base lubricant composition
EP0140274A2 (de) * 1983-10-28 1985-05-08 Röhm Gmbh Additive für Schmieröle

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5218202B2 (ja) * 1971-09-16 1977-05-20
JPS5148153B2 (ja) * 1972-09-30 1976-12-18
US4081385A (en) * 1976-11-02 1978-03-28 Texaco Inc. 4-Vinylpyridine polymethacrylate containing lube oil compositions

Patent Citations (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2114233A (en) * 1933-05-22 1938-04-12 Rohm & Haas Polymeric materials
US2091627A (en) * 1934-06-08 1937-08-31 Rohm & Haas Composition of matter and process
US2100993A (en) * 1934-12-14 1937-11-30 Rohm & Haas Process for preparing esters and products
US2655479A (en) * 1949-01-03 1953-10-13 Standard Oil Dev Co Polyester pour depressants
US3067163A (en) * 1958-05-22 1962-12-04 Rohm & Haas Preparation of detergent oil-additive graft copolymers by delayed addition of nitrogen-containing comonomer to a partially polymerized long chain alkyl or vinyl ester and product obtained thereby
US3226326A (en) * 1962-07-30 1965-12-28 Shell Oil Co Lubricating composition
US3238133A (en) * 1962-07-30 1966-03-01 Shell Oil Co Lubricating oil compositions containing neutral ashless polymeric detergents
US3598736A (en) * 1967-08-30 1971-08-10 Shell Oil Co Polyalkylmethacrylates as pour point depressants for lubricating oils
US3679644A (en) * 1967-08-30 1972-07-25 Shell Oil Co Polyalkylmethacrylates as pour point depressants for lubricating oils
US3607749A (en) * 1967-12-05 1971-09-21 British Petroleum Co Viscosity index improvers
US3869396A (en) * 1971-05-05 1975-03-04 Shell Oil Co Lubricating oil compositions
DE2258966A1 (de) * 1971-12-03 1973-06-07 Shell Int Research Schmieroelgemische
US3833501A (en) * 1971-12-22 1974-09-03 Burmah Oil Trading Ltd Lubricating compositions
US3788990A (en) * 1971-12-22 1974-01-29 J Elliott Lubricating compositions
US3951929A (en) * 1972-05-08 1976-04-20 Texaco Inc. Polyacrylates and waxy residual fuel compositions thereof
US3817866A (en) * 1972-11-24 1974-06-18 Texaco Inc Alkylacrylate alkanediol methacrylate interpolymers and pour depressed compositions thereof
US4073738A (en) * 1976-01-28 1978-02-14 Basf Aktiengesellschaft Lubricating oil compositions containing alkyl acrylate or methacrylate polymers and copolymers of styrene and conjugated diene
US4149984A (en) * 1977-09-08 1979-04-17 Rohm Gmbh Lubricating oil additives
GB1559952A (en) * 1977-10-26 1980-01-30 Shell Int Research Lubricating oil compositions
US4282132A (en) * 1978-08-11 1981-08-04 Rohm Gmbh Lubricating oil additives
US4290925A (en) * 1979-02-16 1981-09-22 Rohm Gmbh Lubricating oil additives
US4332689A (en) * 1979-09-28 1982-06-01 Nippon Oil And Fats Co., Ltd. Water base lubricant composition
EP0140274A2 (de) * 1983-10-28 1985-05-08 Röhm Gmbh Additive für Schmieröle

Non-Patent Citations (4)

* Cited by examiner, † Cited by third party
Title
Hughes et al., J. Applied Polymer Science, V, 15, 337 348 (1961). *
Hughes et al., J. Applied Polymer Science, V, 15, 337-348 (1961).
Olabisi et al., Polymer Polymer Miscibility, Academic Press, New York 1979, p. 233. *
Olabisi et al., Polymer-Polymer Miscibility, Academic Press, New York 1979, p. 233.

Cited By (48)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4968444A (en) * 1983-10-28 1990-11-06 Rohm Gmbh Lubricating oil additives
US5043087A (en) * 1986-04-25 1991-08-27 Rohn Gmbh Addives for paraffinic lubricants
US5035822A (en) * 1986-06-13 1991-07-30 Institut Francais Du Petrol Copolymer compositions particularly useful as additives for hydrocarbon oils
US4921625A (en) * 1988-06-27 1990-05-01 Shell Oil Company Method for preparing functionalized block copolymers
US5349019A (en) * 1988-12-24 1994-09-20 Hoechst New copolymers, mixtures thereof with poly(meth)acrylate esters and the use thereof for improving the cold fluidity of crude oils
US5188770A (en) * 1989-09-09 1993-02-23 Rphm GmbH Viscosity index improver having detergent properties
US5073600A (en) * 1989-10-12 1991-12-17 Shell Oil Company Dispersant viscosity index improvers
EP0436872A3 (en) * 1990-01-12 1991-09-11 Roehm Gmbh Mineral oil based transmission fluid
EP0436872A2 (de) * 1990-01-12 1991-07-17 Röhm GmbH Kraftübertragungsflüssigkeit auf Basis Mineralöl
RU2102402C1 (ru) * 1990-12-14 1998-01-20 Министеро делл Юниверсита е делла Ричерка Шентифика е Текнологика Полимерная присадка, улучшающая индекс вязкости, способ ее получения, мономер, обладающий диспергирующим действием, концентрат и смазочное масло
US5534175A (en) * 1992-12-28 1996-07-09 The Lubrizol Corporation Copolymers of unsaturated fatty esters, their use as viscosity improver and lubricating oil containing said copolymers
AU674927B2 (en) * 1992-12-28 1997-01-16 Lubrizol Corporation, The Copolymers of unsaturated fatty esters, their use as viscosity improver and lubricating oil containing said copolymers
US5368761A (en) * 1993-04-30 1994-11-29 Rohm And Haas Company Copolymer useful as a pour point depressant for a lubricating oil
US5416162A (en) * 1993-09-20 1995-05-16 Rohm And Haas Company Compatibilizer for a viscosity index improving polymer blend
US5622924A (en) * 1994-03-08 1997-04-22 Sanyo Chemical Industries, Ltd. Viscosity index improver and lubricating oil
US5665685A (en) * 1994-06-02 1997-09-09 Sanyo Chemical Industries, Ltd. Gear and transmission lubricant compositions of improved sludge-dispersibility, fluids comprising the same
US5696066A (en) * 1994-10-12 1997-12-09 Rohm And Haas Company Additive for lubricating oil
KR100405388B1 (ko) * 1994-10-19 2004-02-11 아깊페트롤리쏘시에떼퍼아 찌오니 불소탄성중합체와 상용성인 윤활유용 다기능성 첨가제
US5520832A (en) * 1994-10-28 1996-05-28 Exxon Research And Engineering Company Tractor hydraulic fluid with wide temperature range (Law180)
US6294628B1 (en) 1995-06-19 2001-09-25 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US5821313A (en) * 1995-06-19 1998-10-13 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US6639034B2 (en) 1995-06-19 2003-10-28 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US6331603B1 (en) 1995-06-19 2001-12-18 The Lubrizol Corporation Nitrogen containing acrylic copolymers
US5969068A (en) * 1995-06-19 1999-10-19 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US6881780B2 (en) 1995-06-19 2005-04-19 The Lubrizol Corporation Dispersant-viscosity improvers for lubricating oil compositions
US5807815A (en) * 1997-07-03 1998-09-15 Exxon Research And Engineering Company Automatic transmission fluid having low Brookfield viscosity and high shear stability
EP0889114A1 (en) * 1997-07-03 1999-01-07 Exxon Research And Engineering Company Automatic transmission fluids having low Brookfield viscosity and high shear stability
EP0937769A1 (en) * 1998-02-18 1999-08-25 The Lubrizol Corporation Viscosity improvers for lubricating oil compositions
US6271184B1 (en) 1998-12-22 2001-08-07 The Lubrizol Corporation Viscosity improvers for lubricating oil-compositions
US6124249A (en) * 1998-12-22 2000-09-26 The Lubrizol Corporation Viscosity improvers for lubricating oil compositions
US7378379B2 (en) * 2003-06-10 2008-05-27 The Lubrizol Corporation Functionalized polymer composition for grease
US20040254080A1 (en) * 2003-06-10 2004-12-16 The Lubrizol Corporation, A Corporation Of The State Of Ohio Functionalized polymer composition for grease
US7947636B2 (en) 2004-02-27 2011-05-24 Afton Chemical Corporation Power transmission fluids
EP1619235A1 (en) * 2004-07-21 2006-01-25 Afton Chemical Limited Polyalkylmethacrylate polymer as filtration improver
US20060019841A1 (en) * 2004-07-21 2006-01-26 Nicholas Clague Oil additive
KR100714141B1 (ko) 2004-07-21 2007-05-02 에프톤 케미칼 코포레이션 C12-20 폴리알킬 메트아크릴레이트 중합체의 윤활제 첨가제로서의 용도
US8163683B2 (en) 2007-06-08 2012-04-24 Toho Chemical Industry Co., Ltd. Pour point depressant for lubricant
US20100120641A1 (en) * 2007-06-08 2010-05-13 Toho Chemical Industry Co., Ltd. Pour point depressant for lubricant
CN101679902B (zh) * 2007-06-08 2013-06-12 东邦化学工业株式会社 润滑油用倾点下降剂
US9051529B2 (en) 2009-06-04 2015-06-09 The Lubrizol Corporation Lubricating composition containing friction modifier and viscosity modifier
CN102858928A (zh) * 2010-04-26 2013-01-02 赢创罗曼克斯添加剂有限公司 传动系统用润滑剂
US9481849B2 (en) 2010-04-26 2016-11-01 Evonik Oil Additives Gmbh Polymer useful as viscosity index improver
US9617495B2 (en) 2010-04-26 2017-04-11 Evonik Oil Additives Gmbh Transmission lubricant
WO2013062924A2 (en) 2011-10-27 2013-05-02 The Lubrizol Corporation Lubricating composition containing an esterified polymer
US20150075061A1 (en) * 2013-09-17 2015-03-19 Vanderbilt Chemicals, Llc Method of reducing aqueous separation in an emulsion composition suitable for engine fueled by e85 fuel
US9550952B2 (en) * 2013-09-17 2017-01-24 Vanderbilt Chemicals, Llc Method of reducing aqueous separation in an emulsion composition suitable for engine fueled by E85 fuel
US20220372388A1 (en) * 2019-12-12 2022-11-24 Evonik Operations Gmbh High viscosity polyacrylate base fluids
US11965140B2 (en) * 2019-12-12 2024-04-23 Evonik Operations Gmbh High viscosity polyacrylate base fluids

Also Published As

Publication number Publication date
JP2509199B2 (ja) 1996-06-19
EP0225598A2 (de) 1987-06-16
EP0225598A3 (en) 1988-10-12
CA1288411C (en) 1991-09-03
EP0225598B1 (de) 1991-08-14
DE3680880D1 (de) 1991-09-19
JPS62141096A (ja) 1987-06-24
DE3544061A1 (de) 1987-06-19

Similar Documents

Publication Publication Date Title
US4822508A (en) Shear stable multirange oils having an improved viscosity index
US4867894A (en) Pour point improving additives for mineral oils
US4968444A (en) Lubricating oil additives
JP2732187B2 (ja) 無灰分散剤ポリメタクリレート重合体
US4146492A (en) Lubricant compositions which exhibit low degree of haze and methods of preparing same
CA2357474C (en) Dispersant (meth) acrylate copolymers having excellent low temperature properties
JP4391014B2 (ja) 高−及び低分子量ポリマー添加剤混合物を用いる潤滑油の低温流動性の改良法
AU605594B2 (en) Nitrogen-free esters of carboxy containing interpolymers
CA2276900C (en) (meth)acrylate copolymers having excellent low temperature properties
CA2448520C (en) Alkyl (meth) acrylate copolymers
US5043087A (en) Addives for paraffinic lubricants
US5622924A (en) Viscosity index improver and lubricating oil
US4606834A (en) Lubricating oil containing VII pour depressant
US3816315A (en) Mineral oil compositions
JP2968347B2 (ja) 作動液
CN102272278A (zh) 含嵌段共聚物的组合物和润滑内燃机的方法
JPH093131A (ja) 潤滑油組成物用の分散剤−粘度改良剤
JPS619497A (ja) 自動変速機油組成物
EP0561335B1 (en) Lubricating oil viscosity index improver composition
AU662159B2 (en) Dispersant poly(meth)acrylate viscosity index improvers
CA2830885A1 (en) Viscosity index improver, lubricant oil additive, and lubricant oil composition
US5726136A (en) Multifunctional additive for lubricating oils compatible with fluoroelastomers
EP0329756B1 (en) Methacrylate pour point depressants and compositions
JP2004525231A (ja) オレフィン共重合体およびアクリル酸エステル共重合体を含有する潤滑剤
US4844829A (en) Methacrylate pour point depressants and compositions

Legal Events

Date Code Title Description
AS Assignment

Owner name: ROHM GMBH, 6100 DARMSTADT, FED. REP. OF GERMANY

Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNORS:PENNEWISS, HORST;JOST, HEINZ;KNOELL, HELMUT;REEL/FRAME:004992/0071

Effective date: 19861128

STCF Information on status: patent grant

Free format text: PATENTED CASE

FEPP Fee payment procedure

Free format text: PAYOR NUMBER ASSIGNED (ORIGINAL EVENT CODE: ASPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 4

FPAY Fee payment

Year of fee payment: 8

FEPP Fee payment procedure

Free format text: PAYER NUMBER DE-ASSIGNED (ORIGINAL EVENT CODE: RMPN); ENTITY STATUS OF PATENT OWNER: LARGE ENTITY

FPAY Fee payment

Year of fee payment: 12